US5145971A - Process for the preparation of oxydiphthalic acid and purified oxydiphthalic anhydride from crude oxydiphthalic anhydride - Google Patents
Process for the preparation of oxydiphthalic acid and purified oxydiphthalic anhydride from crude oxydiphthalic anhydride Download PDFInfo
- Publication number
- US5145971A US5145971A US07/783,026 US78302691A US5145971A US 5145971 A US5145971 A US 5145971A US 78302691 A US78302691 A US 78302691A US 5145971 A US5145971 A US 5145971A
- Authority
- US
- United States
- Prior art keywords
- acid
- oxydiphthalic
- anhydride
- water
- process according
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/083—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid anhydrides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/54—Preparation of carboxylic acid anhydrides
- C07C51/56—Preparation of carboxylic acid anhydrides from organic acids, their salts, their esters or their halides, e.g. by carboxylation
Definitions
- This invention relates to a method for converting oxydiphthalic anhydride into purified oxydiphthalic acid.
- the oxydiphthalic acid may be used as a curing agent for epoxy resins, and may be converted into its esters which are useful as plasticizers.
- the purified oxydiphthalic acid may be converted into oxydiphthalic anhydride, which is purer than the oxydiphthalic anhydride starting material.
- Oxydiphthalic anhydride is useful in the production of polyimide resins. Such polyimide resins have a variety of uses, but are often used in electronic application. For electronic use, it is desirable to have oxydiphthalic anhydride of high purity and low ionic concentration.
- Oxydiphthalic anhydride is often prepared from 4-chlorophthalic anhydride by coupling two molecules of the 4-chlorophthalic anhydride to form oxydiphthalic anhydride.
- the crude product of such a coupling reaction often includes organic solvents, unreacted starting material and catalysts, ionic substances, and various colored materials of unknown composition.
- the process of the present invention is useful for the conversion of oxydiphthalic anhydride prepared by the coupling of two molecules of 4-chlorophthalic anhydride into pure oxydiphthalic acid.
- the process is general and may be used to convert impure oxydiphthalic anhydride from any source into pure oxydiphthalic acid.
- the process is particularly useful in preparing oxydiphthalic acid which is converted into oxydiphthalic anhydride for use in the production of polyimides for electronic use.
- Graebe has disclosed in Leibigs Annalen der Chemie Vol. 149, p. 18, 1869, that tetrachlorophthalic acid may be purified by recrystallization from water followed by sublimation. During the sublimation process the acid is converted to the anhydride which may be reconverted to the acid by boiling in water.
- phthalic anhydride may be purified by dissolving in non-aqueous solvent, and passing the solution through a material, capable of absorbing colored impurities, such as charcoal. The solution is filtered and passed through a series of crystallization tanks of successively lower temperatures. Pure phthalic anhydride is obtained in the crystallization tanks maintained at the highest temperature and the impurities are crystallized at lower temperatures.
- phthalic anhydride may be purified by mixing sufficient water with the anhydride to form a slurry, heating the slurry to 375°-400° F., removing the anhydride from the slurry by passing steam into the mixture and condensing the vapors at 300° F. whereby a condensate of phthalic anhydride is produced which is substantially free of water.
- the phthalic anhydride is then further purified by fractional distillation.
- U.S. Pat. No. 2,937,189 discloses that pyromellitic acid, in water solution, may be treated with activated carbon to remove any organic impurities which may be present and treated with a metal extracting agent, e.g., a cation exchange resin to remove any metals which may be present.
- a metal extracting agent e.g., a cation exchange resin
- phthalic anhydride may be purified by passing molten phthalic anhydride over an activated carbon bed.
- U.S. Pat. No. 3,236,885 discloses that pyromellitic acid may be purified by dissolving the acid in water, treating the aqueous solution with activated carbon, separating the carbon from the aqueous solution and recovering the purified pyromellitic acid from the water.
- U.S. Pat. No. 3,338,923 discloses a method of purifying pyromellitic dianhydride by treating the impure dianhydride with ketones.
- the patent also discloses that it is known in the prior art that pyromellitic dianhydride may be purified by converting the dianhydride into the acid with water and recrystallizing the acid from water in the presence of activated carbon.
- oxydiphthalic anhydride can be purified by filtering or centrifuging a hot solution of oxydiphthalic anhydride in a high boiling solvent to remove impurities, followed by cooling the solution to precipitate the oxydiphthalic anhydride, which can be removed from the solution by filtration or centrifuging.
- U.S. Pat. No. 4,906,760 discloses that metal ion impurities may be removed from aromatic anhydrides "by refluxing the anhydride in an aqueous solution to decyclize the anhydride and to ionize or dissolve the metal impurities in the water vehicle, provide an activated adsorption agent such as activated carbon to clarify the solution, filtering off the absorption agent (and recovering the polyacid therefrom by washing the filter cake with warm water for return to the main solution) allowing the solution to stand and cool and precipitate the purified polyacid, filtering and washing the polyacid and finally recyclizing the polyacid back to the purified anhydride.”
- an activated adsorption agent such as activated carbon
- tetrachlorophthalic acid may be purified by dissolving the acid in a water solution containing 2-20% of a water miscible ether such as dioxane, tetrahydofuran and acetals.
- a water miscible ether such as dioxane, tetrahydofuran and acetals.
- the crude tetrachlorophthalic anhydride is dissolved in a mixture of water and the ether and filtered hot. Upon cooling to room temperature, the crystals of acid form which are then washed and dried to form tetrachlorophthalic anhydride.
- U.S. Pat. No. 4,914,231 discloses a method for purifying diphenylsulfone tetracarboxylic acids by dissolving the crude tetracarboxylic acid in a mixture of water and acetic acid and allowing the acid to crystallize in order to obtain a highly purified diphenylsulfone tetracarboxylic acid.
- concentration of acetic acid in the solvent mixture ranges from 2 to 90 volume % and preferably from about 10 to about 70 volume %.
- the crude diphenylsulfone tetracarboxylic acid contains a heavy metal ion
- removal of the heavy metal ion is more effective if the solution is treated with a cation exchange resin, or with oxalic acid prior to crystallization.
- the Examples show that if cation exchange resins or oxalic acid are not used, the heavy metal ion level is not reduced below about 100 ppm.
- the amount of the solvent mixtures relative to the crude diphenyl sulfone is about 1 to 200 times and preferably 3 to 50 times.
- European Patent Number 0 421 046 A1 discloses a process for producing highly pure 3,3',4,4'-biphenyl tetra-carboxylic acid or the dianhydride thereof.
- the 3,3',4,4'-biphenyltetracarboxylic acid is heated at a temperature of 160° to 260° C. in order to drive off certain impurities.
- the acid is cyclized to the anhydride.
- the anhydride is then treated with hot water at a temperature of 95° to 105° C.
- certain impurities dissolve in the water and the anhydride is converted to the acid. If the anhydride is the desired product, it may be reformed by heating the tetraacid.
- crude oxydiphthalic anhydride may be treated with a mixture of water and propionic acid or butyric acid to form purified oxydiphthalic acid.
- the most effective composition range for the water-acid mixture is from about 25% acid to 75% acid.
- the resulting oxydiphthalic acid may be cyclized to form oxydiphthalic anhydride.
- crude oxydiphthalic anhydride is treated with an aqueous solution of either propionic or butyric acid.
- This treatment produces oxydiphthalic acid which is substantially purer than the crude oxydiphthalic anhydride from which it is prepared.
- the present process removes organic solvents, unreacted starting materials and catalysts, ionic substances, and various colored materials of unknown composition.
- the oxydiphthalic acid produced may be dehydrated (cyclized) to form oxydiphthalic anhydride which is substantially purer than the crude oxydiphthalic anhydride starting material.
- the process may be used as a method of converting crude oxydiphthalic anhydride into purified oxydiphthalic acid.
- the process may be used as a method of purifying oxydiphthalic anhydride.
- mixtures of water and either propionic or butyric acid function better, in applicant's process, than mixtures with either acetic or formic acids.
- Propionic acid is the preferred acid for use in the present invention. While butyric acid provides good results, its use is not preferred because of its well-known odor.
- the oxydiphthalic acid produced by the present process leads, after cyclization, to a purer grade of oxydiphthalic anhydride. Thus, the process may be used to produce a purified grade of oxydiphthalic acid or oxydiphthalic anhydride.
- the process of the present invention is not a classical recrystallization.
- a classical recrystallization method the material to be purified is dissolved in a solvent, often at an elevated temperature, and the solution is filtered. After filtration, the filtrate is cooled, or concentrated, and the purified material crystallizes out of the solution.
- the present process begins with a slurry of crude oxydiphthalic anhydride in an aqueous solvent. As the mixture is heated, the entire slurry may dissolve, to form a solution which may remain clear for a brief period. The formation of a clear solution is unpredictable.
- a clear solution is more likely to form than is the case at high ratios.
- a super-saturated solution of oxydiphthalic acid may form. Crystallization of the oxydiphthalic acid in such a solution would occur fairly quickly. However, such a solution might occasionally remain clear for a brief period. Whatever the reasons may be for the occasional appearance of a clear solution, a filtration cannot reliably be done in the present process. A clear solution may not form, and if it does form, it is not likely to remain clear for a sufficient period of time to accomplish a filtration.
- the mixture of oxydiphthalic anhydride in the aqueous phase is warmed to a temperature of between about 40° C. and the reflux temperature, at atmospheric pressure, of the aqueous solvent.
- a temperature of between about 40° C. and the reflux temperature, at atmospheric pressure, of the aqueous solvent At the lower temperatures in the range, the hydrolysis of the oxydiphthalic anhydride to the oxydiphthalic acid is somewhat slow, and the process takes longer. Whatever temperature is selected, the mixture is held at that temperature until the anhydride is substantially hydrolyzed. In practice, the mixture is held for a longer period of time in order to assure that the hydrolysis is, in fact, complete.
- the present process is conducted with a slurry rather than with a solution. Accordingly, there is no opportunity in the present process for hot filtration of the solution of the product to be purified. Since the process does not involve a step of hot filtration of a solution of the oxydiphthalic acid, there is no possibility for using adsorption agents within the process. Thus, if one were to add a material such as silica gel, or activated carbon, it could not be removed by filtration and would show up in the final product.
- the process of the present invention removes colored materials without the use of adsorption agents such as charcoal.
- adsorption agents are not required by the present process is a major advantage since the initial cost of the charcoal is saved and the process does not produce a charcoal waste stream which must either be purified and recycled or disposed of as a waste.
- a filtration step for removal of the adsorption agent is not required.
- Aqueous mixtures of the appropriate concentration provide better purification than is provided by a solvent mixture containing either more of the carboxylic acid or less than the optimum range.
- the preferred range of composition of the aqueous mixture is 25 to 75 weight percent acid in water.
- the most preferred concentration range based on color improvement for the solvent is about 40-60% by weight acid in water.
- the process may be conducted at rather high loading of oxydiphthalic anhydride to the aqueous phase.
- the loading is defined as the weight fraction of oxydiphthalic anhydride in the mixture.
- a loading of oxydiphthalic anhydride is typically in the range of 25 to 40%.
- the process provides a pure product.
- such operation is not desirable since it can result in the loss of product remaining in the large volume of solvent.
- the large volumes of aqueous phase would add to the cost of the process.
- the lowest practical limit for conducting the process would probably be a loading of oxydiphthalic anhydride of approximately 10%.
- the liquid and solid phases are separated.
- the separation may be accomplished by any of the methods known by those skilled in the art, such as filtration or centrifuging.
- a washing step is optional, especially when large quantities of solvent compared to the amount of oxydiphthalic acid are used. However, the use of a wash is definitely preferred because it helps to remove the solvent from the oxydiphthalic acid and thereby lessens the chance for accidental re-introduction of impurities into the acid.
- Either a water wash or a wash consisting of a propionic acid and water mixture may be used.
- the wash solution may vary in composition from pure water to approximately 75% by weight propionic acid in water. If an acid wash is chosen, the preferred range is 25 to 75% propionic acid. It is preferred to use a cold wash solution in order to avoid the loss of the oxydiphthalic acid which could dissolve in the wash solution. We have found that somewhat better color properties are obtained if a mixture of propionic acid and water is used as a washing solution.
- the oxydiphthalic acid may be recyclized (dehydrated) to form oxydiphthalic anhydride.
- recyclization There are many methods of accomplishing recyclization which are well-known to those skilled in the art.
- one method is treatment of the oxydiphthalic acid with acetic anhydride.
- the acetic anhydride is converted to acetic acid and the oxydiphthalic acid is converted to the anhydride.
- Other chemical reagents have been used to remove the water to reform the anhydride.
- the oxydiphthalic acid may be treated with a hot, high boiling solvent in which water is immiscible.
- the water formed by recyclization distills out along with the solvent, is separated from the solvent, and thereby removed from the process.
- the oxydiphthalic acid may be melted and cooled.
- oxydiphthalic anhydride if formed.
- a convenient method of cyclization which has been used is to heat the oxydiphthalic acid in a dryer at a temperature of 200°-220° C. for several hours in order to remove the water and form the dianhydride. Since the process of purification works equally well with any method of cyclization of the dianhydride, a person skilled in the art may readily select a cyclization method which best fits his needs.
- ODPA oven-dried oxydiphthalic anhydride
- ODPA oven-dried oxydiphthalic anhydride
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Furan Compounds (AREA)
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US07/783,026 US5145971A (en) | 1991-10-25 | 1991-10-25 | Process for the preparation of oxydiphthalic acid and purified oxydiphthalic anhydride from crude oxydiphthalic anhydride |
EP19920107903 EP0538547A3 (en) | 1991-10-25 | 1992-05-11 | Process for the preparation of oxydiphthalic acid and purified oxydiphthalic anhydride from crude oxydiphthalic anhydride |
JP4216881A JPH0798774B2 (ja) | 1991-10-25 | 1992-08-14 | 粗オキシジ無水フタル酸からオキシジフタル酸及び精製オキシジ無水フタル酸の調製方法 |
CN92112232A CN1043757C (zh) | 1991-10-25 | 1992-10-20 | 氧代二邻苯二甲酸和其纯化的酸酐的制备方法 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US07/783,026 US5145971A (en) | 1991-10-25 | 1991-10-25 | Process for the preparation of oxydiphthalic acid and purified oxydiphthalic anhydride from crude oxydiphthalic anhydride |
Publications (1)
Publication Number | Publication Date |
---|---|
US5145971A true US5145971A (en) | 1992-09-08 |
Family
ID=25127954
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US07/783,026 Expired - Lifetime US5145971A (en) | 1991-10-25 | 1991-10-25 | Process for the preparation of oxydiphthalic acid and purified oxydiphthalic anhydride from crude oxydiphthalic anhydride |
Country Status (4)
Country | Link |
---|---|
US (1) | US5145971A (fr) |
EP (1) | EP0538547A3 (fr) |
JP (1) | JPH0798774B2 (fr) |
CN (1) | CN1043757C (fr) |
Cited By (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5336788A (en) * | 1993-11-15 | 1994-08-09 | Occidental Chemical Corporation | Method of making oxydiphthalic anhydride |
US20060135791A1 (en) * | 2004-12-22 | 2006-06-22 | General Electric Company | Method of purifying dianhydrides |
US20060293528A1 (en) * | 2005-06-24 | 2006-12-28 | General Electric Company | Method of purifying dianhydrides |
US20070073063A1 (en) * | 2005-09-23 | 2007-03-29 | General Electric Company | Method for purifying bisimides |
US20070073035A1 (en) * | 2005-09-23 | 2007-03-29 | General Electric Company | Method for making polyetherimides |
US20070117990A1 (en) * | 2005-11-22 | 2007-05-24 | General Electric Company | Method of purifying dianhydrides |
WO2008063207A1 (fr) * | 2006-11-22 | 2008-05-29 | Sabic Innovative Plastics Ip B.V. | Procédé de purification de dianhydrides |
WO2008082413A1 (fr) * | 2007-01-04 | 2008-07-10 | Sabic Innovative Plastics Ip B.V. | Procédé de purification de dianhydrides |
US20080281073A1 (en) * | 2004-12-07 | 2008-11-13 | Mitsubishi Chemical Corporation | High-Purity Oxydiphthalic Acid Anhydride and Process for Producing the Same |
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WO2004096787A1 (fr) * | 2003-04-28 | 2004-11-11 | Mitsubishi Chemical Corporation | Lactones polycycliques, (meth)acrylates presentant des structures de lactones polycycliques, et leur procede de production |
JP2004359669A (ja) * | 2003-04-28 | 2004-12-24 | Mitsubishi Chemicals Corp | 多環式ラクトン化合物及び多環式ラクトン構造を有する(メタ)アクリレート化合物、並びにその製造方法 |
CN108392899B (zh) * | 2018-03-15 | 2020-08-18 | 濮阳市盛源石油化工(集团)有限公司 | 一种脱除1,2-环己烷二甲酸的装置及其工艺 |
CN114349727B (zh) * | 2022-01-25 | 2022-11-22 | 河北海力香料股份有限公司 | 一种降低3,3’,4,4’-二苯醚二酐合成中醋酸残留的方法 |
CN114478233B (zh) * | 2022-02-09 | 2023-03-28 | 河北海力恒远新材料股份有限公司 | 一种二苯醚四甲酸的精制方法、一种二苯醚二酐的制备方法 |
CN115073405B (zh) * | 2022-07-27 | 2023-08-15 | 河北海力恒远新材料股份有限公司 | 一种超痕量高纯联苯醚二酐的制备方法 |
Citations (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
SU160176A1 (fr) * | ||||
US1301388A (en) * | 1918-06-29 | 1919-04-22 | Courtney Conover | Process for the purification of crude phthalic anhydrid. |
US2786805A (en) * | 1954-03-01 | 1957-03-26 | California Research Corp | Process of purification of phthalic anhydride |
US3338923A (en) * | 1965-03-24 | 1967-08-29 | Gelsenberg Benzin Ag | Process of purifying pyromellitic dianhydride |
US3540987A (en) * | 1967-07-07 | 1970-11-17 | Metallgesellschaft Ag | Purification of phthalic anhydride by batch distillation,accumulation and continuous distillation |
US3650906A (en) * | 1968-04-13 | 1972-03-21 | Zieren Chemiebau Gmbh Dr A | Thin film heating for the preliminary purification of crude phthalic anhydride |
US3850967A (en) * | 1971-04-05 | 1974-11-26 | Gulf Research Development Co | Purification of benzophenone tetracarboxylic dianhydride using a silica containing adsorbent |
US3869479A (en) * | 1970-02-07 | 1975-03-04 | Zieren Chemiebau Gmbh Dr A | Removal of impurities during the recovery of crude phthalic anhydride |
US4215051A (en) * | 1979-08-29 | 1980-07-29 | Standard Oil Company (Indiana) | Formation, purification and recovery of phthalic anhydride |
DE3339392A1 (de) * | 1983-10-29 | 1985-05-09 | Davy McKee AG, 6000 Frankfurt | Verfahren zum beheizen und kuehlen eines phthalsaeureanhydrid-abscheiders und anlage zur abscheidung von phthalsaeureanhydrid |
US4906760A (en) * | 1988-08-04 | 1990-03-06 | Hoechst Celanese Corp. | Purification of anhydrides |
US4914231A (en) * | 1987-09-19 | 1990-04-03 | New Japan Chemical Co., Ltd. | Method for purifying a crude diphenylsulfone tetracarboxylic acid |
US4948921A (en) * | 1989-06-29 | 1990-08-14 | Amoco Corporation | Process for the production and recovery of trimellitic acid |
JPH09199683A (ja) * | 1996-01-22 | 1997-07-31 | Sanyo Electric Co Ltd | 半導体装置の製造方法 |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4900865A (en) * | 1987-11-25 | 1990-02-13 | Amoco Corporation | Method for producing a di-(mono- or poly-)carboxyaryl ether |
US4808731A (en) * | 1988-03-04 | 1989-02-28 | General Electric Company | Method for making oxydiphthalic anhydride |
-
1991
- 1991-10-25 US US07/783,026 patent/US5145971A/en not_active Expired - Lifetime
-
1992
- 1992-05-11 EP EP19920107903 patent/EP0538547A3/en not_active Ceased
- 1992-08-14 JP JP4216881A patent/JPH0798774B2/ja not_active Expired - Lifetime
- 1992-10-20 CN CN92112232A patent/CN1043757C/zh not_active Expired - Fee Related
Patent Citations (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
SU160176A1 (fr) * | ||||
US1301388A (en) * | 1918-06-29 | 1919-04-22 | Courtney Conover | Process for the purification of crude phthalic anhydrid. |
US2786805A (en) * | 1954-03-01 | 1957-03-26 | California Research Corp | Process of purification of phthalic anhydride |
US3338923A (en) * | 1965-03-24 | 1967-08-29 | Gelsenberg Benzin Ag | Process of purifying pyromellitic dianhydride |
US3540987A (en) * | 1967-07-07 | 1970-11-17 | Metallgesellschaft Ag | Purification of phthalic anhydride by batch distillation,accumulation and continuous distillation |
US3650906A (en) * | 1968-04-13 | 1972-03-21 | Zieren Chemiebau Gmbh Dr A | Thin film heating for the preliminary purification of crude phthalic anhydride |
US3869479A (en) * | 1970-02-07 | 1975-03-04 | Zieren Chemiebau Gmbh Dr A | Removal of impurities during the recovery of crude phthalic anhydride |
US3850967A (en) * | 1971-04-05 | 1974-11-26 | Gulf Research Development Co | Purification of benzophenone tetracarboxylic dianhydride using a silica containing adsorbent |
US4215051A (en) * | 1979-08-29 | 1980-07-29 | Standard Oil Company (Indiana) | Formation, purification and recovery of phthalic anhydride |
DE3339392A1 (de) * | 1983-10-29 | 1985-05-09 | Davy McKee AG, 6000 Frankfurt | Verfahren zum beheizen und kuehlen eines phthalsaeureanhydrid-abscheiders und anlage zur abscheidung von phthalsaeureanhydrid |
US4914231A (en) * | 1987-09-19 | 1990-04-03 | New Japan Chemical Co., Ltd. | Method for purifying a crude diphenylsulfone tetracarboxylic acid |
US4906760A (en) * | 1988-08-04 | 1990-03-06 | Hoechst Celanese Corp. | Purification of anhydrides |
US4948921A (en) * | 1989-06-29 | 1990-08-14 | Amoco Corporation | Process for the production and recovery of trimellitic acid |
JPH09199683A (ja) * | 1996-01-22 | 1997-07-31 | Sanyo Electric Co Ltd | 半導体装置の製造方法 |
Cited By (17)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5336788A (en) * | 1993-11-15 | 1994-08-09 | Occidental Chemical Corporation | Method of making oxydiphthalic anhydride |
US20080281073A1 (en) * | 2004-12-07 | 2008-11-13 | Mitsubishi Chemical Corporation | High-Purity Oxydiphthalic Acid Anhydride and Process for Producing the Same |
US20060135791A1 (en) * | 2004-12-22 | 2006-06-22 | General Electric Company | Method of purifying dianhydrides |
US7495113B2 (en) * | 2004-12-22 | 2009-02-24 | Sabic Innovative Plastics | Method of purifying dianhydrides |
US20060293528A1 (en) * | 2005-06-24 | 2006-12-28 | General Electric Company | Method of purifying dianhydrides |
US20070073035A1 (en) * | 2005-09-23 | 2007-03-29 | General Electric Company | Method for making polyetherimides |
US7408070B2 (en) | 2005-09-23 | 2008-08-05 | Sabic Innovative Plastics Ip B.V. | Method for purifying bisimides |
US7411032B2 (en) | 2005-09-23 | 2008-08-12 | Sabic Innovative Plastics Ip B.V. | Method for making polyetherimides |
US7446214B2 (en) | 2005-09-23 | 2008-11-04 | Sabic Innovative Plastics Ip B.V. | Method for purifying oxybisphthalic anhydrides |
US20080319210A1 (en) * | 2005-09-23 | 2008-12-25 | Albert Santo Stella | Method for purifying dianhydrides |
US20070073063A1 (en) * | 2005-09-23 | 2007-03-29 | General Electric Company | Method for purifying bisimides |
US8134016B2 (en) | 2005-09-23 | 2012-03-13 | Sabic Innovative Plastics Ip B.V. | Method for purifying dianhydrides |
US20070117990A1 (en) * | 2005-11-22 | 2007-05-24 | General Electric Company | Method of purifying dianhydrides |
US7863463B2 (en) | 2005-11-22 | 2011-01-04 | Sabic Innovative Plastics Ip B.V. | Method of purifying dianhydrides |
WO2008063206A1 (fr) * | 2006-11-21 | 2008-05-29 | Sabic Innovative Plastics Ip B.V. | Procédé de production de polyétherimides |
WO2008063207A1 (fr) * | 2006-11-22 | 2008-05-29 | Sabic Innovative Plastics Ip B.V. | Procédé de purification de dianhydrides |
WO2008082413A1 (fr) * | 2007-01-04 | 2008-07-10 | Sabic Innovative Plastics Ip B.V. | Procédé de purification de dianhydrides |
Also Published As
Publication number | Publication date |
---|---|
JPH06287161A (ja) | 1994-10-11 |
JPH0798774B2 (ja) | 1995-10-25 |
CN1073436A (zh) | 1993-06-23 |
EP0538547A3 (en) | 1993-05-12 |
EP0538547A2 (fr) | 1993-04-28 |
CN1043757C (zh) | 1999-06-23 |
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